Acetic Acid → HCID 21966284, compound

HRID 2212462Notes

Reaction equation

HRID 2212462 reaction equation
[OH:1][CH2:2][C:3]([CH3:14])([CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[C:15](O)(=[O:17])[CH3:16]>O.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[C:15]([O:1][CH2:2][C:3]([CH3:14])([CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8])(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 21966285HCID 21966285, compound

Product 1

HCID 21966284HCID 21966284, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 962WaterSolvent

Procedure

Into a 100 mL round-bottom flask equipped with a magnetic spin bar and a glass stopper was added 6-hydroxymethyl-6-methyl-1,10-undecadiene (9.41 g, 48 mmol), glacial acetic acid (60.1 g, 1.0 mol) and scandium (III) triflate (1.23 g, 2.5 mmol). The mixture was stirred at ambient temperature for approximately 10 minutes and a colorless solution was obtained. The reaction mixture was stirred for an additional 24 hours at ambient temperature. The reaction mixture was then transferred into a 500 mL separatory funnel and diluted with 100 mL of deionized water. The solution was extracted with three 50 mL portions of methylene chloride. The combined methylene chloride extracts were washed with two 100 mL portions of deionized water, 100 mL of saturated sodium bicarbonate, 100 mL of brine and finally dried over anhydrous magnesium sulfate. The excess methylene chloride was removed with a rotary evaporator to afford a light oil. The oil was distilled under vacuum to afford 9.39 g of 6-acetoxymethyl-6-methyl-1,10-undecadiene (bp=66 to 71° C./8.7 Pa). The FTIR, 13C and 1H nmr were consistent with the proposed structure.

Workup

  1. customInto a 100 mL round-bottom flask equipped with a magnetic spin bar
  2. customa colorless solution was obtained
  3. stirringThe reaction mixture was stirred for an additional 24 hours at ambient temperature
  4. customThe reaction mixture was then transferred into a 500 mL separatory funnel
  5. extractionThe solution was extracted with three 50 mL portions of methylene chloride
  6. washThe combined methylene chloride extracts were washed with two 100 mL portions of deionized water, 100 mL of saturated sodium bicarbonate, 100 mL of brine
  7. dry with materialfinally dried over anhydrous magnesium sulfate
  8. customThe excess methylene chloride was removed with a rotary evaporator
  9. customto afford a light oil
  10. distillationThe oil was distilled under vacuum

Sources & evidence

ORD record
ord-c80fd23ad4994869a4e333b0576f7410
Source dataset
uspto-grants-2006_09
Patent number
US07101956B2

Reaction notes

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